# US 11,305,267 B2 · Catalyst for preparing high purity taurine and use thereof

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- Number: US 11,305,267 B2
- Document ID: US11305267B2
- Status: Granted
- Kind: B2
- Application number: 17/369,963
- Filed: 2021-07-08
- Published: 2021-10-28
- Granted: 2022-04-19
- Earliest claimed: 2019-07-01
- Assignees: Hubei Grand Life Science and Technology Co., Ltd.
- Applicants: Hubei Grand Life Science and Technology Co., Ltd
- Inventors: Huajun Sun; Shangjin Yang; Ruyong Jiang; Chen Guo; Zhiqiang Qian
- Web page: https://patentgrep.com/patent/US11305267B2

## CPC

- B01J 31/0237: {Amines}
- B01J 31/0271: {also containing elements or functional groups covered by B01J31/0201 - B01J31/0231}
- B01J 31/0225: {comprising sulfonic acid groups or the corresponding salts}
- C07C 303/22: from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups}
- C07C 303/32: of salts of sulfonic acids
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Provided is a catalyst for preparing high-purity taurine, and the catalyst is N,N-disubstituted aminoethanesulfonic acid and has a structure represented by Formula I, in which R1 and R2 are each independently selected from alkyl, alkenyl, alkynyl, alkoxy, benzyl, sulfhydryl, thioether group, aryl, heteroaryl, amino, amide, imide, cyano, aldehyde group, carbonyl, carboxyl, sulfonic acid group, or ester group. Also provided is a method for preparing high-purity taurine, which adds the catalyst in an ammonolysis step for preparing taurine, thereby having effects of high yield, inhibition of impurity production and a reduced amount of ammonia used, etc. The catalyst has advantages of low cost, stable physical properties, and easy separation from the product. The preparation method is simple to operate with easily available raw materials and high yield, and can be employed for industrial production. Moreover, the purity of the prepared taurine can be up to 98% or higher.

## Claims

### Claim 1

A method for preparing taurine, comprising using a catalyst having a structure represented by Formula I in an ammonolysis process of the method,
wherein R1 and R2 are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, sulfhydryl, a thioether group, aryl, heteroaryl, amino, an amide group, an imide group, cyano, an aldehyde group, carbonyl, carboxyl, a sulfonic acid group, an ester group, and combinations thereof; and X is selected from H, a metal element of group IA, or a metal element of group IIA;
the alkyl is a linear or branched saturated C1-C18 hydrocarbyl;
the alkenyl is selected from linear or branched alkenyl groups containing at least one C═C double bond and 2 to 12 carbon atoms;
the alkynyl is selected from linear or branched alkynyl groups containing at least one C≡C triple bond and 2 to 12 carbon atoms;
the alkoxy is selected from linear or branched C1-C6 alkoxy;
the thioether group is selected from a methyl sulfide group or an ethyl sulfide group;
the aryl is selected from phenyl or substituted phenyl, wherein the substituted phenyl means that at least one hydrogen on a benzene ring is substituted by a substituent selected from a hydrogen isotope, halogen, cyano, nitro, carboxyl, an ester group, unsubstituted methylthio, methylthio substituted with 1 to 3 fluorine atoms, C1-C8 alkyl, or C1-C8 alkoxy;
the heteroaryl is selected from a five- to seven-membered monocyclic aromatic ring containing at least one heteroatom or an eight- to twelve-membered bicyclic aromatic ring containing at least one heteroatom, wherein the at least one heteroatom is selected from N, O or S, and the rest are carbon;
the amide group is an amide group substituted with a linear or branched C1-C18 alkyl;
the imide group is an imide group substituted with a linear or branched C1-C18 alkyl;
the carbonyl is alkoxycarbonyl; and
the ester group is selected from an ester group substituted with a linear or branched C1-C18 alkyl, an aryl ester group, or a carboxylic ester group.

### Claim 2 (depends on 1)

The method according to claim 1, comprising:
step S1 of performing a hydroxylation reaction of ethylene oxide and sodium bisulfite to produce sodium isethionate;
step S2 of performing ammonolysis of the sodium isethionate under effect of one or more catalysts represented by Formula I; and
step S3 of neutralizing a product of the ammonolysis to obtain the taurine.

### Claim 3 (depends on 2)

The method according to claim 2, comprising:
step S1 of reacting ethylene oxide with a sodium bisulfite solution to produce sodium isethionate;
step S2 of mixing the sodium isethionate obtained in step S1 with ammonia, adding the one or more catalysts to obtain a reaction solution, performing an ammonolysis reaction at high temperature and high pressure, discharging excess ammonia from the reaction solution through flash evaporation after the ammonolysis reaction is completed, then discharging the remaining ammonia and excess water through evaporation, and recycling the ammonia discharged through the flash evaporation and the evaporation as a raw material for the ammonolysis reaction;
step S3 of acidifying a reaction solution obtained after the evaporation in step S2 through direct acidification, ion exchange or electrolysis/electroosmosis to replace sodium ions in molecules of sodium taurinate with hydrogen ions; and
separating the taurine from the unreacted sodium isethionate and the one or more catalysts through solid-liquid separation to obtain a solid product of the taurine.

### Claim 4 (depends on 2)

The method according to claim 2, wherein a molar ratio of the one or more catalysts to the sodium isethionate ranges from 0.1% to 15%.

### Claim 5 (depends on 3)

The method according to claim 3, wherein a molar ratio of the one or more catalysts to the sodium isethionate ranges from 0.1% to 15%.

### Claim 6 (depends on 2)

The method according to claim 2, wherein a molar ratio of the ammonia to the sodium isethionate ranges from 0.1:1 to 50:1; and/or
the ammonia is provided in a form of ammonia water at a concentration ranging from 20% to 35%, based on a total mass of the ammonia water; and/or
the ammonolysis reaction continues for 0.1 h to 40 h.

### Claim 7 (depends on 3)

The method according to claim 3, wherein a molar ratio of the ammonia to the sodium isethionate ranges from 0.1:1 to 50:1; and/or
the ammonia is provided in a form of ammonia water at a concentration ranging from 20% to 35%, based on a total mass of the ammonia water; and/or
the ammonolysis reaction continues for 0.1 h to 40 h.

### Claim 8 (depends on 6)

The method according to claim 6, wherein a molar ratio of the ammonia to the sodium isethionate ranges from 6:1 to 8:1; and/or
the ammonia is provided in a form of ammonia water at a concentration ranging from 25% to 35%, based on a total mass of the ammonia water; and/or
the ammonolysis reaction continues for 1.5 h to 2 h.

### Claim 9 (depends on 7)

The method according to claim 7, wherein a molar ratio of the ammonia to the sodium isethionate ranges from 6:1 to 8:1; and/or
the ammonia is provided in a form of ammonia water at a concentration ranging from 25% to 35%, based on a total mass of the ammonia water; and/or
the ammonolysis reaction continues for 1.5 h to 2 h.

### Claim 10 (depends on 3)

The method according to claim 3, wherein an acid used in the direct acidification comprises organic acids, inorganic acids, acidic gases, and acidic polymer compounds;
the acidifying through ion exchange comprises cation exchange, anion exchange, and combined anion and cation exchange; and
the acidifying through the electrolysis/electroosmotic comprises direct electrolysis, electrodialysis, and bipolar membrane electrodialysis.

### Claim 11 (depends on 1)

The method according to claim 1, wherein
the alkenyl is selected from linear or branched alkenyl groups containing at least one C═C double bond and 2 to 8 carbon atoms;
the alkynyl is selected from linear or branched alkynyl groups containing at least one C≡C triple bond and 2 to 8 carbon atoms;
the alkoxy is selected from methoxy, ethoxy, propoxy, or isopropoxy;
the heteroaryl is selected from pyrrolyl, thienyl, indolyl, or benzofuranyl;
the amide group is acetylamino;
the imide group is acetylimido; and
the carbonyl is selected from methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl.

### Claim 12 (depends on 11)

The method according to claim 11, wherein
the alkyl is a linear or branched saturated C1-C6 hydrocarbyl;
the alkenyl is selected from vinyl, propenyl, or isopropenyl; and
the alkynyl is selected from ethynyl, propynyl, or butynyl.

### Claim 13

A method for preparing taurine, comprising using a catalyst having a structure represented by any one of Formula II to Formula V in an ammonolysis process of the method,
wherein in the structure represented by Formula II, R3 and R4 are each independently selected from saturated or unsaturated C1-C20 hydrocarbyl, or saturated or unsaturated C1-C20 alkoxy; and X is selected from H, a metal element of group IA, or a metal element of group IIA;
wherein R5 and R6 are the same or different from each other, and are each independently selected from saturated or unsaturated C1-C18 hydrocarbyl; and X is selected from H, a metal element of group IA, or a metal element of group IIA;
wherein R7 is selected from hydrogen, saturated or unsaturated C1-C20 hydrocarbyl, or saturated or unsaturated C1-C20 alkoxy; and X is selected from H, a metal element of group IA, or a metal element of group IIA;
wherein R8 is selected from hydrogen, or saturated or unsaturated C1-C18 hydrocarbyl; and X is selected from H, a metal element of group IA, or a metal element of group IIA.

### Claim 14 (depends on 13)

The method according to claim 13, wherein
in the structure represented by Formula II, R3 and R4 are the same or different from each other, and are each independently selected from saturated or unsaturated C1-C10 hydrocarbyl;
in the structure represented by Formula III, R5 and R6 are the same or different from each other, and are each independently C1-C12 alkyl;
in the structure represented by Formula IV, R7 is selected from hydrogen or saturated or unsaturated C1-C10 hydrocarbyl; and
in the structure represented by Formula V, R8 is selected from saturated or unsaturated C1-C12 hydrocarbyl and X is H.

### Claim 15 (depends on 14)

The method according to claim 14, wherein
R5 and R6 are the same or different from each other, and are each independently C8-C12 alkyl;
R7 is hydrogen or methyl; and
R8 is methyl, ethyl or dodecyl.

### Claim 16 (depends on 13)

The method according to claim 13, wherein X is sodium.

### Claim 17 (depends on 16)

The method according to claim 16, wherein the catalyst has a structure represented by any one of Formula III, Formula IV, or Formula V, wherein X is sodium.

### Claim 18 (depends on 13)

The method according to claim 13, wherein the catalyst is any one selected from the following structures:
or N-dodecylamino-N,N-bis(2-ethanesulfonic acid).